In 1988, Traylor joined the WWF, who modified his Big Bubba Rogers
ring name to that of the "Big Bossman", based on his previous
profession. Wrestling as a heel and managed by Slick,
Bossman's post-match gimmick involved handcuffing his defeated
opponents (mainly jobbers) to the ring rope and beating them with a
nightstick.

After defeating Koko B. Ware at the inaugural SummerSlam, Bossman made his first major WWF impact when he attacked Hulk Hogan on Brother Love's interview segment. During his feud with Hogan, Bossman also challenged for the WWF Championship, held by Randy "Macho Man" Savage; and began teaming with Akeem to form the Twin Towers. As the Twin Towers, Bossman and Akeem feuded mainly with Hogan and Savage (who had formed The Mega Powers
alliance), and were strongly involved in the storyline involving
Savage's slowly building heel turn and eventual betrayal of Hogan. The
Twin Towers were The Mega Powers' opponents the night of Savage's turn;
Hogan, who was abandoned by his partner late in the match, rallied to
defeat the Twin Towers.

In 1992, Bossman became involved in a feud with Nailz,
whose gimmick was that of an ex-convict; in a series of promos that
aired before his debut, Nailz claimed to be abused by Bossman during his
incarceration, and warned that he was coming for revenge. During a
television taping that aired May 30, Nailz — clad in an orange prison
jumpsuit — ran into the ring and attacked the Bossman, handcuffing him
to the top rope and repeatedly choking and beating him with the
nightstick. Bossman eventually recovered and went after Nailz in a
series of matches during the latter half of 1992. The feud culminated
when Bossman defeated Nailz in a Nightstick on a Pole match at Survivor Series.

After leaving the WWF in 1993, Traylor had a brief stint in All Japan Pro Wrestling, where he was paired up with Stan Hansen and "Dr. Death" Steve Williams, before returning to the United States to work for World Championship Wrestling.
He made his WCW debut on WCW Saturday Night in December 1993 by pinning
the International World Champion Ravishing Rick Rude in a non-title
match. He received a World title shot against Rick Rude at Starrcade '93
with Rude retaining the title. Traylor was originally known as The
Boss, but the WWF legal department determined the character to be too
similar to the one that Traylor had portrayed in the WWF and forced WCW
to change it. As a result, Traylor became the Guardian Angel. He feuded with Big Van Vader for most of 1994. Soon, Traylor turned heel and returned to his original Big Bubba Rogers character. He defeated Sting at Uncensored in March 1995. Big Bubba joined the Dungeon of Doom faction before eventually defecting to the nWo.
Eventually, a loophole in Bubba's contract forced him out of the nWo.
As a result of this, Bubba became a face once again and began competing
under his real name—Ray Traylor and was briefly managed by old nemesis
Ted Dibiase, who also recently left the nWo. He frequently worked with the Steiner Brothers during this time period. He began feuding with the nWo, defeating several nWo members such as Scott Hall, Curt Hennig, and Vincent.

Eventually, Traylor returned to the WWF on the October 12, 1998 episode of Raw is War, once again under his Big Bossman persona. However, his character
was changed from a regular police officer to a bully-type personal
security officer, or bodyguard-type character, willing to do anything
for a price. The change was further emphasized by his new SWAT-style
attire and considerable weight loss prior to appearing on television.
Traylor was immediately established as a top of the mid-card character,
as he was introduced as a member of The Corporation, a group of
wrestlers controlled by WWF owner Vince McMahon to combat Stone Cold Steve Austin as well as D-Generation X, as The Corporation's "personal security". During his time as a member of The Corporation, Bossman won the Tag Team Championship with Ken Shamrock and won the Hardcore Championship four times. While still a member of the Corporation, Bossman competed at WrestleMania XV against Undertaker in a Hell in a Cell match, which he lost. Undertaker subsequently "hung" Bossman inside the cage, leaving him suspended in the air.

Most of his matches in the hardcore division were part of his feud with Al Snow. At one point, the storyline involved Al's dog Pepper. At SummerSlam,
the pair fought in a match that never made it to the ring; it instead
spilled into the backstage area, the street, and finally into a nearby
bar. Just prior to the match, Snow was seen setting Pepper's dog carrier
near the entrance way. Minutes into the match, Boss Man picked up the
carrier, taunted the dog, struck Snow with the carrier, and carelessly
tossed it behind him. Announcer Jim Ross apologized immediately for the stunt, and confirmed on air that Pepper had been removed from the box before the match.

Two weeks later, Pepper was taken out of the storyline when he was, in storyline killed by the Bossman, who then tricked Snow into eating his pet. The storyline concluded with a Kennel from Hell match at Unforgiven.
The cage surrounded the ring, with a second roofed cage surrounding the
ringside area. The men would start in the ring, with the first man to
escape both cages being declared the winner. Between the two cages were a
number of attack dogs.

After this, he feuded with The Big Show over the WWF Championship. The feud included a monologue where Bossman showed up at Big Show's father's storyline
funeral (his father had actually died years earlier) and proceeded to
steal Show's father's casket by rigging it to the back of his car and
driving off. In a desperate attempt to stop the theft, The Big Show
jumped onto the coffin as it was being towed away, riding atop the
coffin for a few yards until he lost his grip and tumbled off. Bossman
became the #1 contender for the WWF Championship on the November 15,
1999 edition of Raw. This feud ended with Boss Man being defeated by Big Show at the Armageddon pay-per-view.

In the summer of 2000, Bossman disappeared from mainstream WWF television and wrestled mainly on Jakked and Heat, primarily feuding with Crash Holly. When Traylor returned from an injury in late 2001, he was given a role as the tag team partner of Booker T, as simply The Boss Man. Boss Man served as an enforcer again, only this time for Booker T under the order of Vince McMahon. The team quietly split in late January 2002, and from there on Boss Man wrestled mostly on Jakked and Heat. In April, he formed a short lived tag team with Mr. Perfect after both were drafted to the Raw brand. In May 2002, he competed in his last WWE match, losing to Tommy Dreamer. Traylor was then assigned to train new wrestlers in Ohio Valley Wrestling before being released from WWE in 2003.

Following his departure from WWE, Traylor's last series of matches were in a tournament for the vacant International Wrestling Association of Japan heavyweight title. He made it all the way to the finals before being defeated by old rival Jim Duggan. Traylor's last match came a week before his death against The Tonga Kid for Ted DiBiase's promotion in Arizona. Traylor appears in the WWE All Stars video game as a downloadable character.